82830-36-2

Upstream product

• 80304-50-3 1-benzyl-5-hydroxymethylimidazole 
• 39123-65-4 3-benzyl-2-thioxotetrahydro-4H-imidazol-4-one 
• 287198-16-7 3-benzyl-2-(methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one 
• 1609282-78-1 1-benzyl-2-(methylthio)-5-imidazolcarbonitrile 
• 91025-37-5 ethyl 3-benzyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-4-carboxylate 
• 100-44-7 benzyl chloride 
• 1399859-85-8 N-benzyl-N'-(2'-acetamido)thiourea 
• 76075-21-3 ethyl 1-benzyl-1H-imidazole-5-carboxylic acid 
• 160999-35-9 1-Benzyl-5-(2-phenylethenyl)-1H-imidazole 
• 85102-99-4 1-benzyl-1H-imidazole-5-carboxaldehyde 
• 60293-41-6 N-((E)-3-phenylallylidene)benzylamine 

Downstream Products

• 1256643-67-0 2-(1-benzyl-1H-imidazol-5-yl)acetonitrile 
• 160999-36-0 (2S,5R)-2-<(1-Benzylimidazol-5-yl)methyl>-2,5-dihydro-3,6-dimethoxy-5-isopropylpyrazine 

Relevant academic research and scientific papers

Preparation of 2'-13c-l-histidine starting from 13c-thiocyanate: Synthetic access to any site-directed stable isotope enriched l-histidine

1-Benzyl-2-(methylthio)-imidazole-5-ketone is obtained in a few simple steps starting from thiocyanate and glycine amide (glycin). Subsequent treatment with diethyl phosphorocyanidate and functional group manipulations gives 1-benzyl-5-chloromethylimidazolium chloride. This compound is converted under mild O'Donnell conditions into the corresponding L-histidine derivative. After deprotection L-histidine is obtained in good yield and 99% enantiomeric excess. 2'-13C-L-Histidine has been obtained via this new scheme with high (99%) 13C incorporation starting with commercially available 13C- thiocyanate. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives.

Synthesis of L-histidine specifically labelled with stable isotopes

(2'-13C)-, (1'-15N)- and (3'-15N)-L-Histidine were prepared according to a synthetic scheme that allows the 13C or 15N labelling of all carbon and nitrogen positions or any combination of positions.A 1,5-disubstituted imidazole ring was constructed via condensation of tosylmethyl isocyanide with 3-phenylpropenal and subsequent cycloaddition of benzylamine.The imidazole intermediate was converted into 1-benzyl-5-(chloromethyl)-imidazolium chloride which was coupled to a glycine moiety via an enantioselective coupling with the bislactim ether of cyclo-D-valylglycine.Deprotection of the coupling product afforded L-histidine in high optical purity.Syntheses for the isotopically labelled synthons were developed starting from simple, comercially available, highly enriched compounds.The labelled L-histidines were characterized by mass spectrometry and 1H-, 13C- and 15N-NMR spectroscopy.